Trail Homes with Check With District Elementary school

Welcome to Trail, Oregon – a hidden gem nestled in the heart of Jackson County! This charming city offers a unique blend of natural beauty and community spirit, making it an ideal place for families, outdoor enthusiasts, and anyone looking to embrace a serene lifestyle.

Surrounded by the majestic Cascade Mountains and lush forests, Trail is a paradise for nature lovers. With an abundance of hiking trails, fishing spots, and opportunities for wildlife viewing, residents can easily immerse themselves in the great outdoors. The scenic landscape is complemented by the tranquil waters of the nearby Rogue River, providing a perfect backdrop for weekend adventures or peaceful afternoons spent by the water.

In addition to its natural allure, Trail boasts a close-knit community that prioritizes family and education. The local schools, including the well-regarded Check With District Elementary, are committed to fostering a nurturing environment for young learners. Parents can rest easy knowing their children are receiving quality education just a stone’s throw from home, making this area particularly appealing for families.

Real estate in Trail offers a variety of charming homes, from cozy cabins to spacious family residences. Many properties feature stunning views and easy access to outdoor activities, ensuring that every day feels like a vacation. Whether you’re looking to settle down or invest in a vacation home, Trail presents a fantastic opportunity to enjoy a peaceful lifestyle in a picturesque setting.

Come discover the welcoming community and breathtaking landscapes of Trail, Oregon – where your dream home awaits!

Newest Trail Homes with Check With District Elementary school

$559,000

3 Beds ⋅ 3 Baths ⋅ 220221847 MLS

Escape to your private 10+ acre wilderness sanctuary! This grand log home perfectly blends rustic luxury with ultimate functionality. The property backs up to BLM land for unmatched privacy & boasts spectacular, views of the Cascade Mtns. Inside find breathtaking, open-beam vaulted ceilings and a warm, inviting living space centered around a brick-surrounded pellet stove. The highly versatile floor plan offers 2 spacious main-level bdrms. Upstairs, discover a privately tucked-away primary suite complete with an en-suite bath and flexible loft area. Large, functional kitchen features abundant storage, walk-in pantry, and an adjacent dedicated laundry room. The exterior features an oversized garage with built-in shop area, plus dedicated RV parking. Embrace outdoor living on the massive, 932 sq ft covered porch, perfect for morning coffee or sunset views. A dream property for hobbyists, outdoor enthusiasts and travelers alike!

275 Citadel Road, Trail

$335,000

220221427 MLS

Beautiful mountain land bordering USA land, giving you a larger backyard for hunting, hiking and nice buffer from anyone else. Just minutes to Shady Cove which has your shopping, medical, dentist, library and all things needed for comfort. Also, at the gateway to all things recreational. This 20+- homesite has electric, well with abundant water and septic all ready for you. Enjoy the quiet seclusion and whispering pines of the great North West. Just minutes to the Rogue River and Lost Creek Lake for fishing, rafting, hiking and on the way to Crater Lake' you couldn't ask for a nicer place to live. Final lot size will be provided in legal lot survey prior to close of escrow. Additional lots contiguous to this if you want family nearby or community type living, private access to property.

3860 Highway 227, Trail

$499,000

4 Beds ⋅ 2 Baths ⋅ 220219353 MLS

Beautifully updated 4-bedroom, 2-bath home offering 2,025 sqft on 3.92 private acres in a peaceful forest setting with fruit trees, gated entry, RV parking, and a circular (roundabout) driveway. Nearly every major component has been upgraded--new roof, siding, paint, windows, decks, gutters, and exterior lighting with security cameras. Enjoy peace of mind with a new breaker box, power drop, meter base, well pump, pressure tank, and 2,500-gallon water storage system. Inside features modern comfort with PEX plumbing, remodeled bathrooms, fresh interior paint, new flooring (carpet & LVP), updated lighting, new kitchen cabinets, appliances, and added laundry. Detached double-wide carport included. Seller willing to sell mostly furnished (minus a few items). A rare turnkey property combining privacy, space, and extensive upgrades--move-in ready!

6481 Highway 227, Trail

$699,900

2 Beds ⋅ 3 Baths ⋅ 220216483 MLS

Fisherman's retreat or potential short term rental income on the world-famous Rogue River! This prime riverfront prop. offers a beautiful setting w/seasonal Salmon/Steelhead runs right out your back door. Rolling low-bank frontage/your own private boat launch, and concrete dock perfect for relaxing/taking in the river/forest. Home is already updated - upgraded LVP floors/barn doors/newer roof/paint/cabinets, a newly built expansive deck w/plenty of space for entertaining, and a functional kitchen w/dining area overlooking the large yard and river. Detached 2nd bedroom/office w/half bath. functional multi-space shop, w/additional carport/RV pkg/fenced dog run/mature landscaping complete the package. Minutes to Shady Cove/Lost Creek Lk./hunting/hiking/rafting/vineyards/endless recreation/short jaunt Crater Lk. Natl. Park. Might make great 2nd home, seasonal retreat, Air BNB or primary Res.

24990 Highway 62, Trail

$519,900

3 Beds ⋅ 2 Baths ⋅ 220211814 MLS

Freshly remodeled 3-bedroom, 2-bath home featuring 1,911-sq. ft. of spacious, open living filled with natural light! Enjoy breathtaking mountain views and abundant wildlife from every room. The home offers a new kitchen with butcher block counters, freshly updated bathrooms, laminate flooring throughout, wood-burning fireplace, expansive decking, durable metal roof, and new mini splits for year-round comfort. Plenty of room for all your toys, projects, and hobbies on 21.51-private acres. The property backs up to over 2,500-acres of public lands, providing endless opportunities for hunting, trail riding, hiking, and outdoor recreation in every season. Just 7 minutes from Shady Cove, this home combines privacy, comfort, and adventure, making it a true nature lover's paradise where every day feels like a getaway.

5015 Highway 227, Trail

$440,000

220210917 MLS

Two Tax lots creating 100-acre sloped, forested parcel located in the scenic Trail, OR area. Zoned OSR (Open Space Reserve), offering potential for recreation, conservation, or low-impact development. Check with Jackson County for Home Site Development process. An adjacent 80-acre parcel is also available and can be combined for expanded use or access. Buyer to perform own Due Diligence regarding intended use for the property.

Loper Lane, Trail

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The content relating to real estate for sale on this site comes in part from the IDX program of the RMLS of Portland, Oregon. Real Estate listings held by brokerage firms other than this firm are marked with the RMLS logo, and detailed information about these properties include the name of the listing's broker. Listing content is copyright © 2026 RMLS of Portland, Oregon. All information provided is deemed reliable but is not guaranteed and should be independently verified. This content last updated on . Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.

The data relating to real estate for sale on this web site comes in part from the Internet Data Display (IDX) of the Southern Oregon Multiple Listing Service. Real estate listings held by brokerage firms other than our company are marked with the IDX logo and detailed information about them includes the name of the listing brokers. The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information subject to change and should be independently verified. Listing content is copyright © 2018 SOMLS, Medford, Oregon. Last updated: